Hey,I’m transitioning from single-family to multi-family investments and looking for a comprehensive, practical course.

This book was released in 2019 but I found it to contain a lot of great information on voucher programs.https://www.amazon.com/Subsidized-Comprehensive-Government-F...

Based on the value of a property you can likely get away with a inexpensive desk top study such as condos and you will require a more comprehensive engineering study for larger properties like a 4plex.Desktop / modeling options are sometimes good for smaller residential like you mention. 

Your question in (1), my simplest answer is this is why you're not ready to be a Managing Broker, your lack of knowledge, insight and comprehension in this regard. 

I've been using Avail to generate leases and collect payments from guests for my MTR but I don't think it has comprehensive enough features. 

Not all are comprehensive or even right, it is buyer beware.

When you find out the present zoning of the property, the future land use and the local agencies comprehensive plan for how they see the area being developed (all can be done at the local planning office) you will have a much better idea of what you have just bought.If the land could in any way be developed into something more than single family residential lots, i.e. if there is any multi-family or commercial component than I would advise you to hire someone qualified to help you with the site planning of the development.

A financial advisor can help you  create a comprehensive financial plan to make sure you cover all your bases before you move forward. 

Their familiarity with the local market and diverse financial products could be beneficial.Huntington Bank: With a significant presence in Ohio, Huntington Bank provides various commercial banking solutions and has a history of working with business clients, including those with complex ownership structures.PNC Bank: As a major regional bank, PNC offers comprehensive commercial banking services and has experience dealing with corporate clients, which may align with your fund's requirements.It's advisable to contact these banks directly to discuss your specific needs and assess their ability to accommodate your investment structure without personal guarantees.

Specifically, you should do a deal only because the (complete, comprehensive, accurate) numbers tell you to do so, not because the calendar tells you to.